Every workplace has its fair share of strange requests, but sometimes bosses cross the line from demanding to downright impossible. These aren’t just stories of working late or handling a tough project, they’re moments when managers asked employees to do things that made no sense at all.
From things physically not possible to do to downright unprofessional petitions. These requests left workers stunned, frustrated, or laughing in disbelief. Some were exhausting, others bizarre, and a few completely out of touch with reality. Yet they all share one thing in common: they reveal just how far some bosses will go when they think authority means anything goes.
1
Boss asked me to dress in a clown suit and rainbow wig for a kids’ party. I refused.
2
While I was on vacation 3,000 miles away, he wanted me to call in every day for updates and to solve all his problems.
3
After working my 9–5, my boss asked me to cover his daughter’s 5–12 shift because she wanted to see the last Twilight movie.
4
At Taco Bell, my manager told me to dig through trash for receipts so we could fill out surveys ourselves with perfect reviews. I was 17 and actually did it.
5
A coworker was told by our boss to sell his car only because it looked nicer than the boss’s.
6
He asked me to climb the shelves to put up stickers that literally said not to climb the shelves because it was dangerous.
7
My boss wanted me to dumpster dive to retrieve something personal she had accidentally thrown away.
8
“Go sweep the rain in the parking lot.” It was during an ongoing thunderstorm.
9
He bought a goat to eat with his family, but his wife objected having it home, he brought it to work and asked me to take it with me until it was grown. No pay offered.
10
My area manager told me to work six months straight with no days off until he “found a new manager.” I burned out and quit on the spot.
11
I was given a split shift between two workplaces, 90 km apart, with only an hour between.
12
The most impossible request. He asked me to work the weekend, for free.
13
I was told to decorate two commercial trucks and create a float for kids in two days, with no budget and no materials but lights and generators. I'm not a magician.
14
As an underwriter, I was forced on a business trip with the sales team. While stuck at the airport, my boss told me to find a public terminal and review sensitive applications with social security numbers.
15
After firing me, the owner of where I worked texted me the next morning asking me to come back and “show her how to do everything.”
